Hydrochloric Acid → HCID 123280337, compound

The mixture of 12 (1.53 g, 5.68 mmol), Pd2(dba)3 (260 mg, 5% mmol), P(t-Bu)3 (0.23 mL, 1 M in toluene, 4% mmol) in dry toluene (30 mL) was stirred under N2 protection for 15 min. Then a solution of LHMDS in toluene (6.2 mL, 1 M in toluene, 6.2 mmol) was added dropwise. After stirred at ambient temperature overnight, the resultant dark color suspension was added 1 N hydrochloric acid (8 mL) slowly. The resulting mixture was stirred at ambient temperature for 2 hours. Then the suspension was filtered through celite and the filtrate was diluted with dichloromethane (70 mL). The organic layer was washed with saturated NaHCO3 aqueous solution, brine, and dried over Na2SO4. After filtered and concentrated, the crude product was purified by silica gel column using hexane and ethyl acetate (2:1) as eluent to give 1.03 g light yellow solid, in 90% yield. 1H NMR (400 MHz, CDCl3): δ 7.58 (d, J=15.9 Hz, 1H), 7.35 (d, J=8.48 Hz, 2H), 6.65 (d, J=8.56 Hz, 2H), 6.22 (d, J=15.9 Hz, 1H), 5.12 (seq, J=6.24 Hz, 1H), 3.91 (brs, 2H), 1.30 (d, J=6.24 Hz, 6H); 13C NMR (100 MHz, CDCl3): δ 167.20, 148.56, 144.55, 129.80, 124.88, 114.84, 114.35, 67.32, 22.00. mp 78-80° C. IR v (Diamond, cm−1): 3417, 3335, 1673, 1592, 1513, 1264, 1168, 1104, 980, 823. MS (ESI) m/z found 206.2 (M+H)+.

1. stirringAfter stirred at ambient temperature overnight
2. stirringThe resulting mixture was stirred at ambient temperature for 2 hours
3. filtrationThen the suspension was filtered through celite
4. additionthe filtrate was diluted with dichloromethane (70 mL)
5. washThe organic layer was washed with saturated NaHCO3 aqueous solution, brine
6. dry with materialdried over Na2SO4
7. filtrationAfter filtered
8. concentrationconcentrated
9. customthe crude product was purified by silica gel column

ORD record

ord-103646617f3f4c128e3eef58f77b0eae

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946254B2